NPASS Compound

Structure

CID20339 OpenBabel06191715342D 43 44 0 0 1 0 0 0 0 0999 V2000 2.0586 5.0233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0586 5.0233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5586 4.1573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5586 4.1573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0586 3.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0586 3.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5586 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5586 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0586 1.5592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0586 1.5592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5586 0.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5586 0.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7930 -1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7065 -1.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9840 -0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0586 -0.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5155 -1.6309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 -1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0586 -0.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2381 -1.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1336 -2.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4653 -2.8184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4291 -1.2242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2614 -0.6810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.5586 -1.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9426 -3.3943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7222 -3.4876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0586 -1.9049 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8561 -2.9876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5336 -0.2297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 0.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5586 -1.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8381 -4.3888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8267 -4.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0641 -2.0094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 24 29 1 0 0 0 0 25 32 1 0 0 0 0 25 33 1 0 0 0 0 26 2 1 1 0 0 0 26 42 1 0 0 0 0 27 35 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 6 0 0 0 30 38 1 6 0 0 0 31 39 1 1 0 0 0 32 34 1 0 0 0 0 32 40 1 1 0 0 0 33 30 1 6 0 0 0 33 43 1 0 0 0 0 34 31 1 1 0 0 0 34 43 1 0 0 0 0 35 41 2 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.46
Volume:	661.852
LogP:	7.205
LogD:	4.472
LogS:	-4.917
# Rotatable Bonds:	26
TPSA:	143.75
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.064
Synthetic Accessibility Score:	4.69
Fsp3:	0.886
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.391
MDCK Permeability:	1.0310810466762632e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	97.77389526367188%
Volume Distribution (VD):	1.298
Pgp-substrate:	3.4922752380371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	8.498
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.96
Carcinogencity:	0.053
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.95

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC20339

Natural Product ID:	NPC20339
*Common Name:**	Donnaienin
IUPAC Name:	(2S)-2-methyl-4-[(2R,8S,11S)-2,8,11-trihydroxy-11-[(2R,3R,5S)-3-hydroxy-5-[(1S)-1-hydroxypentadecyl]oxolan-2-yl]undecyl]-2H-furan-5-one
Synonyms:	Donnaienin
Standard InCHIKey:	JTTZQARJVXNGRN-PSLIAIELSA-N
Standard InCHI:	InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-12-13-17-20-30(38)33-25-32(40)34(43-33)31(39)22-21-28(36)18-15-14-16-19-29(37)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26-,28-,29+,30-,31-,32+,33-,34+/m0/s1
SMILES:	CCCCCCCCCCCCCC[C@@H]([C@@H]1C[C@H]([C@H](O1)[C@H](CC[C@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443448
PubChem CID:	21600039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[484995]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[484995]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[484996]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6.6	ug.mL-1	PMID[484996]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	6.7	ug.mL-1	PMID[484996]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.7	ug.mL-1	PMID[484995]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC20339 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1434
0.2-0.3	5499
0.3-0.4	12313
0.4-0.5	12297
0.5-0.6	6980
0.6-0.7	3055
0.7-0.8	701
0.8-0.85	53
0.85-0.9	34
0.9-0.95	72
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC21208
1.0	High Similarity	NPC233551
1.0	High Similarity	NPC280621
1.0	High Similarity	NPC40376
1.0	High Similarity	NPC48338
0.9878	High Similarity	NPC178215
0.9762	High Similarity	NPC239517
0.9756	High Similarity	NPC142117
0.9756	High Similarity	NPC232555
0.9756	High Similarity	NPC107717
0.9756	High Similarity	NPC171174
0.9756	High Similarity	NPC231096
0.9756	High Similarity	NPC134865
0.9756	High Similarity	NPC240695
0.9756	High Similarity	NPC114694
0.9756	High Similarity	NPC103523
0.9756	High Similarity	NPC62118
0.9756	High Similarity	NPC475581
0.9643	High Similarity	NPC473504
0.9643	High Similarity	NPC91067
0.9643	High Similarity	NPC20621
0.9643	High Similarity	NPC318963
0.9643	High Similarity	NPC40066
0.9643	High Similarity	NPC93794
0.9643	High Similarity	NPC477011
0.9643	High Similarity	NPC42598
0.9643	High Similarity	NPC81778
0.9634	High Similarity	NPC103284
0.9634	High Similarity	NPC471567
0.9634	High Similarity	NPC477014
0.9634	High Similarity	NPC120398
0.9634	High Similarity	NPC286338
0.9634	High Similarity	NPC473478
0.9634	High Similarity	NPC283085
0.9634	High Similarity	NPC66346
0.9634	High Similarity	NPC231009
0.9634	High Similarity	NPC110710
0.9634	High Similarity	NPC473669
0.9634	High Similarity	NPC82795
0.9634	High Similarity	NPC473651
0.9634	High Similarity	NPC477013
0.9634	High Similarity	NPC223871
0.9634	High Similarity	NPC329615
0.9634	High Similarity	NPC1083
0.9634	High Similarity	NPC132496
0.9634	High Similarity	NPC107986
0.9634	High Similarity	NPC329838
0.9529	High Similarity	NPC473904
0.9524	High Similarity	NPC473905
0.9524	High Similarity	NPC287164
0.9524	High Similarity	NPC89001
0.9524	High Similarity	NPC169511
0.9524	High Similarity	NPC320569
0.9524	High Similarity	NPC172821
0.9524	High Similarity	NPC151403
0.9524	High Similarity	NPC171135
0.9524	High Similarity	NPC261952
0.9524	High Similarity	NPC81045
0.9524	High Similarity	NPC234077
0.9524	High Similarity	NPC133730
0.9524	High Similarity	NPC61257
0.9524	High Similarity	NPC242364
0.9524	High Similarity	NPC100454
0.9524	High Similarity	NPC320458
0.9524	High Similarity	NPC39754
0.9524	High Similarity	NPC191929
0.9524	High Similarity	NPC274446
0.9518	High Similarity	NPC134807
0.9518	High Similarity	NPC279267
0.9518	High Similarity	NPC134885
0.9518	High Similarity	NPC69082
0.9518	High Similarity	NPC308412
0.9518	High Similarity	NPC219498
0.9518	High Similarity	NPC210218
0.9518	High Similarity	NPC204686
0.9518	High Similarity	NPC477015
0.9518	High Similarity	NPC473687
0.9512	High Similarity	NPC156804
0.9512	High Similarity	NPC163093
0.9412	High Similarity	NPC139418
0.9412	High Similarity	NPC130359
0.9412	High Similarity	NPC477016
0.9412	High Similarity	NPC280612
0.9412	High Similarity	NPC14901
0.9412	High Similarity	NPC477017
0.9405	High Similarity	NPC476583
0.9405	High Similarity	NPC258068
0.9405	High Similarity	NPC20533
0.9398	High Similarity	NPC322529
0.9286	High Similarity	NPC25703
0.9286	High Similarity	NPC132940
0.9286	High Similarity	NPC112685
0.9286	High Similarity	NPC473840
0.9286	High Similarity	NPC47937
0.9286	High Similarity	NPC293136
0.9286	High Similarity	NPC241360
0.9286	High Similarity	NPC282815
0.9286	High Similarity	NPC219652
0.9268	High Similarity	NPC473529
0.9268	High Similarity	NPC73310
0.9268	High Similarity	NPC180363
0.9268	High Similarity	NPC131002
0.9268	High Similarity	NPC329829
0.9268	High Similarity	NPC473780
0.9268	High Similarity	NPC94875
0.9268	High Similarity	NPC475159
0.9268	High Similarity	NPC473712
0.9268	High Similarity	NPC145914
0.9268	High Similarity	NPC11332
0.9268	High Similarity	NPC65930
0.9167	High Similarity	NPC25764
0.9167	High Similarity	NPC182383
0.9167	High Similarity	NPC202055
0.9167	High Similarity	NPC235809
0.9167	High Similarity	NPC39167
0.9167	High Similarity	NPC473156
0.9167	High Similarity	NPC470400
0.9167	High Similarity	NPC39279
0.9167	High Similarity	NPC475268
0.9167	High Similarity	NPC473671
0.9167	High Similarity	NPC77871
0.9167	High Similarity	NPC477018
0.9167	High Similarity	NPC319036
0.9167	High Similarity	NPC100921
0.9167	High Similarity	NPC9678
0.9167	High Similarity	NPC292809
0.9157	High Similarity	NPC144415
0.9157	High Similarity	NPC253801
0.9091	High Similarity	NPC473723
0.9091	High Similarity	NPC473561
0.9091	High Similarity	NPC11456
0.9091	High Similarity	NPC473663
0.9091	High Similarity	NPC475173
0.9059	High Similarity	NPC477010
0.9059	High Similarity	NPC309211
0.8977	High Similarity	NPC473707
0.8953	High Similarity	NPC159750
0.8953	High Similarity	NPC477012
0.8953	High Similarity	NPC473995
0.8953	High Similarity	NPC470401
0.8953	High Similarity	NPC154097
0.8953	High Similarity	NPC473649
0.8667	High Similarity	NPC473520
0.8478	Intermediate Similarity	NPC36954
0.8462	Intermediate Similarity	NPC476300
0.8444	Intermediate Similarity	NPC473619
0.8352	Intermediate Similarity	NPC184463
0.8352	Intermediate Similarity	NPC30515
0.8352	Intermediate Similarity	NPC473321
0.8261	Intermediate Similarity	NPC295204
0.8261	Intermediate Similarity	NPC288240
0.8261	Intermediate Similarity	NPC81419
0.8261	Intermediate Similarity	NPC179746
0.8261	Intermediate Similarity	NPC475912
0.8261	Intermediate Similarity	NPC162205
0.8261	Intermediate Similarity	NPC273579
0.8242	Intermediate Similarity	NPC51004
0.8211	Intermediate Similarity	NPC473326
0.8211	Intermediate Similarity	NPC187268
0.8202	Intermediate Similarity	NPC469483
0.8191	Intermediate Similarity	NPC476315
0.8191	Intermediate Similarity	NPC279621
0.8152	Intermediate Similarity	NPC12172
0.8152	Intermediate Similarity	NPC208886
0.814	Intermediate Similarity	NPC470147
0.814	Intermediate Similarity	NPC133226
0.8132	Intermediate Similarity	NPC307411
0.8132	Intermediate Similarity	NPC295312
0.809	Intermediate Similarity	NPC21469
0.8085	Intermediate Similarity	NPC471142
0.8085	Intermediate Similarity	NPC270013
0.8085	Intermediate Similarity	NPC471141
0.8085	Intermediate Similarity	NPC14961
0.8068	Intermediate Similarity	NPC284472
0.8068	Intermediate Similarity	NPC229799
0.8068	Intermediate Similarity	NPC116543
0.8068	Intermediate Similarity	NPC286770
0.8065	Intermediate Similarity	NPC212486
0.8043	Intermediate Similarity	NPC473448
0.8043	Intermediate Similarity	NPC474232
0.8043	Intermediate Similarity	NPC476004
0.8043	Intermediate Similarity	NPC474761
0.8023	Intermediate Similarity	NPC180725
0.8023	Intermediate Similarity	NPC470148
0.8023	Intermediate Similarity	NPC470149
0.8022	Intermediate Similarity	NPC202672
0.8022	Intermediate Similarity	NPC473715
0.8021	Intermediate Similarity	NPC471144
0.8	Intermediate Similarity	NPC306041
0.8	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC474026
0.8	Intermediate Similarity	NPC477921
0.8	Intermediate Similarity	NPC475711
0.7979	Intermediate Similarity	NPC474035
0.7979	Intermediate Similarity	NPC81386
0.7979	Intermediate Similarity	NPC474247
0.7978	Intermediate Similarity	NPC288471
0.7959	Intermediate Similarity	NPC86077
0.7957	Intermediate Similarity	NPC327760
0.7955	Intermediate Similarity	NPC474959

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC20339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	2175
0.2-0.3	3809
0.3-0.4	2057
0.4-0.5	658
0.5-0.6	220
0.6-0.7	55
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD46	Approved
0.8242	Intermediate Similarity	NPD6698	Approved
0.8	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7838	Discovery
0.7579	Intermediate Similarity	NPD7983	Approved
0.7404	Intermediate Similarity	NPD6686	Approved
0.73	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6371	Approved
0.7196	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4250	Approved
0.6979	Remote Similarity	NPD4251	Approved
0.6875	Remote Similarity	NPD4249	Approved
0.6837	Remote Similarity	NPD1695	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6737	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD5344	Discontinued
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5363	Approved
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3197	Phase 1
0.6562	Remote Similarity	NPD5362	Discontinued
0.6518	Remote Similarity	NPD6053	Discontinued
0.6452	Remote Similarity	NPD4756	Discovery
0.6442	Remote Similarity	NPD7839	Suspended
0.6417	Remote Similarity	NPD7507	Approved
0.6408	Remote Similarity	NPD5282	Discontinued
0.6396	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7829	Approved
0.6387	Remote Similarity	NPD7830	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6435	Approved
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6239	Remote Similarity	NPD7641	Discontinued
0.6224	Remote Similarity	NPD6110	Phase 1
0.6218	Remote Similarity	NPD8033	Approved
0.62	Remote Similarity	NPD5786	Approved
0.6186	Remote Similarity	NPD5369	Approved
0.6172	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8377	Approved
0.6134	Remote Similarity	NPD8294	Approved
0.6102	Remote Similarity	NPD7327	Approved
0.6102	Remote Similarity	NPD7328	Approved
0.61	Remote Similarity	NPD1694	Approved
0.6098	Remote Similarity	NPD3728	Approved
0.6098	Remote Similarity	NPD3730	Approved
0.6083	Remote Similarity	NPD8379	Approved
0.6083	Remote Similarity	NPD8335	Approved
0.6083	Remote Similarity	NPD8378	Approved
0.6083	Remote Similarity	NPD8444	Approved
0.6083	Remote Similarity	NPD8380	Approved
0.6083	Remote Similarity	NPD8296	Approved
0.6082	Remote Similarity	NPD5368	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6412	Phase 2
0.6064	Remote Similarity	NPD8039	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6053	Remote Similarity	NPD6421	Discontinued
0.605	Remote Similarity	NPD7516	Approved
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4790	Discontinued
0.6016	Remote Similarity	NPD8451	Approved
0.6016	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD69	Approved
0.6	Remote Similarity	NPD9119	Approved
0.6	Remote Similarity	NPD2204	Approved
0.5968	Remote Similarity	NPD8448	Approved
0.596	Remote Similarity	NPD5209	Approved
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD7637	Suspended
0.5904	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD4266	Approved
0.5904	Remote Similarity	NPD3194	Approved
0.5904	Remote Similarity	NPD3196	Approved
0.5897	Remote Similarity	NPD8133	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5882	Remote Similarity	NPD7500	Approved
0.5882	Remote Similarity	NPD7505	Discontinued
0.5882	Remote Similarity	NPD9118	Approved
0.5868	Remote Similarity	NPD6319	Approved
0.5865	Remote Similarity	NPD6101	Approved
0.5865	Remote Similarity	NPD5370	Suspended
0.5865	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6845	Suspended
0.5854	Remote Similarity	NPD8328	Phase 3
0.5849	Remote Similarity	NPD6399	Phase 3
0.5827	Remote Similarity	NPD8390	Approved
0.5827	Remote Similarity	NPD8392	Approved
0.5827	Remote Similarity	NPD8391	Approved
0.5826	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7503	Approved
0.5814	Remote Similarity	NPD6109	Phase 1
0.5806	Remote Similarity	NPD8341	Approved
0.5806	Remote Similarity	NPD8342	Approved
0.5806	Remote Similarity	NPD8340	Approved
0.5806	Remote Similarity	NPD7492	Approved
0.5806	Remote Similarity	NPD8299	Approved
0.5794	Remote Similarity	NPD7736	Approved
0.5783	Remote Similarity	NPD3172	Approved
0.578	Remote Similarity	NPD7902	Approved
0.5776	Remote Similarity	NPD2067	Discontinued
0.5772	Remote Similarity	NPD8080	Discontinued
0.5763	Remote Similarity	NPD4632	Approved
0.576	Remote Similarity	NPD6616	Approved
0.5755	Remote Similarity	NPD6411	Approved
0.5755	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6054	Approved
0.5732	Remote Similarity	NPD6927	Phase 3
0.5726	Remote Similarity	NPD6649	Approved
0.5726	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD8293	Discontinued
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6008	Approved
0.5691	Remote Similarity	NPD8267	Approved
0.5691	Remote Similarity	NPD8266	Approved
0.5691	Remote Similarity	NPD8268	Approved
0.5691	Remote Similarity	NPD8269	Approved
0.569	Remote Similarity	NPD6372	Approved
0.569	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD7748	Approved
0.5645	Remote Similarity	NPD6370	Approved
0.5636	Remote Similarity	NPD6083	Phase 2
0.5636	Remote Similarity	NPD6084	Phase 2
0.562	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6059	Approved
0.5603	Remote Similarity	NPD6881	Approved
0.5603	Remote Similarity	NPD7320	Approved
0.5603	Remote Similarity	NPD6899	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data